The Ultimate Guide: What Couples Should Know Before Getting Engaged This Holiday Season

The Ultimate Guide: What Couples Should Know Before Getting Engaged This Holiday Season

The holiday season is basically engagement season. Think about it: twinkling lights, cozy nights by the fire, festive family gatherings—it’s the perfect setting for popping the question. Maybe you’ve even had a few daydreams about your partner down on one knee. (Or, let’s be real, maybe you’ve been secretly sending ring inspo pics for months.)But before you say “yes” and post that ring selfie, there are a few things to consider to make sure you’re setting your future marriage up for success. Engagements are exciting, but they’re also a big deal—it’s not just about the romance but also the commitment, communication, and, yes, even the logistics! Let’s dive into everything you and your partner should know before you officially kick off this next chapter.

The Ultimate Guide: What Couples Should Know Before Getting Engaged This Holiday Season

1. Communication is Everything (Seriously, Everything).

Let’s start with the big one: communication. You’ve probably heard it a thousand times, but it’s the truth—relationships thrive on open and honest conversations. Before you get engaged, sit down with your partner and talk about your future together.

Do you both want kids? What are your career goals? How do you feel about living in the city versus the suburbs? These are the big-picture questions that matter, and it’s better to hash them out now than later. You don’t need to have every single detail figured out, but having a clear idea of your shared vision will make saying “yes” feel even more exciting.

2. Money Talks Aren’t Fun, But They’re Necessary.

Finances can be tricky, but avoiding the conversation won’t make it any easier. Before the proposal, have an honest chat about money—how you handle it, any debts or financial goals, and what kind of budget you’re comfortable with for the engagement ring, wedding, and beyond.

Money disagreements are one of the top reasons couples fight, but talking about it now can save you a lot of stress later. Teamwork is key here—you’re building a life together, and that means figuring out how to handle the dollars and cents as a team.

3. There’s No “Right” Way to Be a Couple.

Every relationship is unique, and the beauty of modern love is that you get to define what works for you. Forget the traditional rulebook (unless that’s your thing!). Instead, talk about your expectations, roles, and how you want to approach your partnership.

Maybe one of you is super organized, and the other is more go-with-the-flow. Maybe you love splitting household chores 50/50, or you’ve got a system where one person cooks while the other does the dishes. Whatever it looks like, make sure it’s built on mutual respect and understanding.

4. Values Matter More Than You Think.

Your shared values are the foundation of your relationship, so make sure you’re aligned on the big stuff. Talk about what’s important to you—things like religion, ethics, or how you plan to handle tough decisions.

Even if you don’t see eye-to-eye on every single belief, having these conversations now will help you understand each other better and avoid major conflicts down the road. Think of it as making sure your compass points in the same direction, even if you take slightly different paths to get there.

5. Don’t Sleep on Pre-marital Counseling.

I know, it might sound old-fashioned, but hear me out. Pre-marital counseling is one of the best ways to strengthen your relationship before you even walk down the aisle.

Think of it like a relationship tune-up. It gives you tools to handle conflict, improve communication, and deepen your connection. Plus, it’s always a good idea to have a neutral third party help guide you through the tricky stuff.

6. Families Can Be… Complicated.

Ah, families—the source of love, laughter, and, occasionally, drama. Getting engaged often means blending two families, and that can be both beautiful and challenging.

Spend some time understanding each other’s family dynamics, traditions, and quirks. Talk about how you’ll navigate holidays, in-laws, and major family events. The key here is respect—respect for your partner, their family, and the way you’ll balance it all as a couple.

7. Learn to Embrace the Art of Compromise.

Spoiler alert: You and your partner aren’t always going to agree on everything. (Shocking, I know.) But learning to compromise is what makes a relationship work.

It’s not about one person always giving in—it’s about finding solutions that make both of you feel heard and respected. Whether it’s deciding on wedding plans or figuring out whose family to visit for Thanksgiving, being flexible will save you so much stress.

Conclusion: Getting engaged during the holiday season is pure magic, but it’s also a chance to lay the groundwork for a happy, healthy marriage. By having honest conversations about communication, money, values, and family, you’ll build a strong foundation for your future together.

Remember, this isn’t just about planning a wedding—it’s about planning a life. And when you’re on the same page with your partner, there’s no limit to what you can create together. So go ahead, pop that champagne, and celebrate—but don’t forget to do the work that makes love last ;)!

Want to plan the perfect proposal this season?Planning and photography is our jam. Book a free discovery call and let’s chat how we can help bring your proposal vision to life!

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The Ultimate Guide: What Couples Should Know Before Getting Engaged This Holiday Season

Wedding Chicks vendor, Hey Honey Photography created this post. Email anna@heyhoneyphotography.com with a link to the post and any credit changes or additions.

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